It’s hard to imagine that 80 years from now, anyone will be interested in paying a hefty admission fee to trudge along a blazing golf green just to view Paris Hilton’s fleshy-pink Bentley Continental, or the one Mercedes SL that Lindsay Lohan failed to wrap around a streetlamp (or pedestrian). But at last week’s Amelia Island Concours d’Elegance, V.F. braved both heat and crowds—not to mention a brutal lurch into Daylight Savings Time—to get up close to a quintet of vehicles that once belonged to some of the most celebrated stars of Hollywood’s (actual) golden era.

We had the pleasure of walking the Concours field with David Gooding, president and founder of the eponymous automotive auction house Gooding & Co. His firm set three dozen world sales records last year in fields like “most expensive car ever sold publicly” (1957 Ferrari 250 Testa Rossa: $16.39 million), so he knows a thing or two about classic-car prices. We asked him if celebrity ownership actually brings value at auction. “It has to be the right car,” he said. “And it has to be the right celebrity.” We think that if these five standout vehicles—all displayed at Amelia this year—ever came across the block, they would all meet at least one, if not both, of these criteria.

Natalie Wood’s 1957 Mercedes 300SL Roadster

Between her starring roles in Rebel Without a Cause (1955) and West Side Story (1961), the 19-year-old Natalie Wood bought one of the earliest Mercedes SL Roadsters—a convertible version of the brand’s groundbreaking Gullwing coupe. Natalie took delivery of the Benz in this gorgeous shade of silvery blue, but immediately had it painted Proto-Hilton pink. A more recent owner returned the car to its original elegance.